


Red Riding Cas

by Winter_Gray



Category: Supernatural
Genre: Humor, M/M, Multi, Sex, Sexy Woodsman Dean, Virgin Castiel, Wolf Sam, three way
Language: English
Status: Completed
Published: 2014-06-07
Updated: 2014-06-23
Packaged: 2018-02-03 17:16:38
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 8,507
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1752551
Author URL: https://archiveofourown.org/users/Winter_Gray/pseuds/Winter_Gray
Summary: <blockquote class="userstuff">
              <p>While traveling through the seamy part of the forest to deliver a basket of goodies for grandpa Bobby, Cas encounters a tall, hot, fuzzy predator. Little Red Riding Cas is pursued by lusty, big bad wolf Sam. Dean is the sexy woodsman trying to save the boy in the tiny red shorts but will Cas end up in a wolf/woodsman sandwich or will Sam claim Cas as his mate?</p>
            </blockquote>





	1. Chapter 1

A/N Any references to Supernatural characters, pop culture products or TV shows are for entertainment purposes only. I don’t make any money off it, don’t own them and its all for fun.  
…………………………….  
Once upon a time there was a boy named Little Red Riding Cas, he was the most adorable, virtuous and sweetest morsel in the entire village of Lupinstein.  
Cas loved the color red and on most days he wore a prim white blouse, little red riding shorts with leather braces, white knee socks and black chucks.  
If the local male population of Lupinstein were lucky they could get a gander at Cas’ wondrously pert butt in the little red shorts as he pranced through the village marketplace.  
It earned him a nickname “Little Red Ride That Ass” of course Cas was never called that to his face.  
He spent his days blissfully unaware that every male he ran across wanted access to his goodie basket which was probably a good thing or Cas would have been afraid to leave his cottage.  
His mother was very cautious and never allowed her son to travel without a rape whistle and a can of bear mace.  
……………….  
In the seamiest region of the forest there lived was a big, bad wolf named Sam. He adored eating boys; the cutest and most virtuous always tasted the best.  
Sam was very tall and handsome with exotic hazel eyes and a mouth full of sharp, white teeth. His glorious mane of hair had two furry little wolf ears poking out and one of them was pierced with a diamond stud.  
His animal magnetism attracted the boys of the village so the wolf never had to snatch pretty things to fill his sexual appetites. The boys came to him for a sound rump pounding but usually ended up with more than they bargained for.  
Little Red Riding Cas remained his elusive prey and Sam wanted to remedy that toot suite.  
……………………  
Dean the Sexy Woodsman, his official title, often saw Cas skipping around the lumberjack camp. The only thing keeping Cas from becoming a party favor to a bunch of horny men was his rape whistle and ever present can of bear mace.  
Dean decided he wanted to get to know the cute little blue eyed fella in the tiny red shorts. He wasn’t sure how he was going to accomplish that since he was written as a minor character. Walk on role or not, Dean was a very determined young man and felt in just a matter of time he would have Cas bent over every available felled tree in a five mile radius.  
………….  
Lupa busied herself loading a picnic basket with tasty treats for her poor sick father Bobby. She called for her son Cas who came prancing right out, “Yes mother what is it?”  
“Cas darling your grandpa Bobby is ill, I’ve packed him a basket with medicine and all sorts of goodies to cheer him up and I want you to skip over there with it as soon as possible,” Lupa tucked a red gingham napkin over the goodies and handed the basket to Cas.  
He stamped his foot in anger, “Darn it Mother, I love grandpa but I always have to listen to his boring old hunting stories and then I end up playing Boggle with him, you know I don’t have a large vocabulary!  
“Don’t worry Cas, today is the Golden Girls marathon on Logo and I’m sure he’d much rather watch that then play Boggle.”  
Cas put on his red cape and took the basket, “That does sound better, grandpa has a crush on Betty White so at least he’ll be in a good mood.”  
“That’s the spirit darling, just be sure grandpa keeps a newspaper on his lap so you’re not grossed out again.”  
Cas bent over to tie his sneakers and Lupa noticed his shorts riding up his butt crack, “I really need to make you new shorts, your fanny hangs out the bottom of these.”  
The boy straightened up and looked over his shoulder, “Mother no one seems to mind at all, if fact many people compliment my little red shorts.”  
Lupa gave a weary sigh, “Someday you’re going to end up on a carton of milk.”  
He gave his mother a big smile, “Because I’m so cute?”  
“Yeah sure, something like that. I swear I’m getting you micro chipped.”  
…………..  
Sam had a pretty young thing bent over a log giving him a sound pound. He growled and grunted as some animals tend to do when they mate with a bitch.  
The boy named Alfie cried out, “My, what a big cock your have!”  
Sam thrust into him again as he cracked Alfie on the ass with a big hand, “The better to poke you with my dear.”  
Big, bad Sam let out a long howl as he finished then pulled out and tossed Alfie his trousers, “Get out of here kid I’m done with your used posterior and if you end up pregnant with a manimal don’t come sniffing around for money. The wolfing business isn’t very lucrative.”  
Alfie stood there with his hands on his hips and snapped, “You are very mean mister wolf!”  
Sam shrugged, “You’re lucky I ate you first,” he ran his tongue over his lips and grinned, “You were delicious but I’m still hungry.”  
The boy ran as fast as he could with naked Sam wolf right behind him.  
……………  
Dean busied himself chopping wood and checking snares since he was a woodsman and all that, “Boy I sure wish I had a bigger role in this story…oh well.”  
Balthazar his fellow woodsman from the lumberjack camp goosed Dean from behind and then pointed to Cas who was skipping down the path through the woods, “Now that is a rabbit worth snaring, I can’t believe you’re not trying to tap that yet.”  
Dean was indignant, “You’re a crude man, I happen to like that boy for his…” he tried to think of something besides the obvious so he didn’t look like a pervert.  
“Brains?”  
“Yeah, brains.”  
They watched as the boy stopped to pick a bouquet of rag weed and skip off again, “Well maybe not brains but I bet he’s super nice!”  
Balthazar snickered and began to walk away; Dean called out, “Where are you going?”  
“That was my cameo role so I’m out of here.”  
Dean watched the lumberjack vanish, “Gee I thought my part was small.”  
…………….  
Cas stopped to pick a bouquet of burdock to add to the ragweed for his grandpa, “Oh grandpa will love these pretty…ouch…prickly purple things.” He wrapped a napkin around them and continued along the path that brought the boy to the seamy parts of the forest.  
He clung to the basket and kept looking around to be sure no wild animals or creepy woodsmen attacked him. Cas rounded a corner where he spotted a big bad wolf.  
Sam was dressed in a pinstripe zoot suit and wearing a fedora with holes cut out to accommodate his ears. Sam twirled his gold pocket watch as he leered at the boy approaching with caution.  
“Hello there pretty little thing, why are you out all alone in such dangerous part of the forest?”  
Cas was going to skip right by but Sam stepped out blocking his path, “I asked you a question sweetheart.”  
Cas dropped his bouquet and clutched his basket of goodies even tighter, “I…I am going to see my grandpa Bobby and bring him this basket of goodies.”  
Sam rubbed the bulge in his pants and growled, “Would you like to see my basket of goodies you frightened little blue eyed…” he bent down and trailed his nose over Cas stopping at his crotch, “virgin boy.” The wolf buried his nose between Cas’ legs and took a deep breath.  
Cas took a step back, “How do you know that?”  
“Mmm…I can smell it on you; your scent is that of cookies and butterscotch. Naughty little whores smell like failure and dirty panties.”  
Red Riding Cas blew his whistle and screamed, “Rapey wolf! Is there no hero to save me?”  
Suddenly someone shouted, “Hey manimal, back away from the virgin!” Dean, excited to make another appearance in the story hurried over waving his arms, “Leave the kid alone you big, hot, delicious, wolf man.”  
Sam eyed the handsome woodsman, “Nice outfit, what are you supposed to be?” Dean placed his boot on a tree stump and adjusted the crotch of his Carhartt jeans, “You’re just jealous because you’d look like crap in flannel.”  
Sam brazenly began sniffing Deans butt, “You’re not a virgin…not a whore…what are you?”  
Dean hitched his thumb toward his chest, “I am Dean the Sexy Woodsman…my official title.”  
Sam growled, “Well Dean, unless you want that little treat in a wolf and woodsman sandwich get out of my story.”  
While they were arguing Cas skipped quickly away to his grandpa’s house.  
……………  
Cas hurried inside and locked the door behind him. Bobby shuffled in wearing a bathrobe, sniffling and dabbing his nose with a handkerchief, “Hello Cas, how is my favorite grandson?”  
Cas hung up his red cape and began unpacking all the goodies and medicine which looked suspiciously like a bottle of whiskey, “I’m your only grandchild so I hope I’m your favorite.”  
Bobby grabbed the bottle, unscrewed the top and took a drink, “Ah your mama sure knows how to cure a cold,” he noticed the nervous expression on his grandsons face, “What’s up boy? You look as if you saw a ghost.”  
“Grandpa, a big, bad wolf stop me in the seamiest part of the forest and I think he wanted to eat me.”  
Bobby rolled his eyes, “I bet it was that fancy pants Sam wolf, yeah he wanted to eat you all right but not in the way you think.” He looked at the tight little red shorts Cas was wearing, “You don’t have any long pants? Those have “eat me” written all over them.”  
Cas tugged the seam out of his butt crack, “No I don’t.”  
Bobby watched out the window at the sun setting, “Stay here tonight, I don’t want my virtuous grandson getting eaten on the way home,” the old man smiled, “besides there’s a Golden Girls marathon on Logo!”  
“Oh yes mother told me, it sounds fun.”  
The grandfather and grandson popped some corn and settled in for evening of television and GILF. Cas tossed his grandfather the newspaper, “Gross.”  
“Sorry kid, you know what Betty White does to me.”  
Outside the window two hazel eyes glowed in the darkness watching the tasty boy curled up on the couch. Behind Sam were two green eyes peering out from the trees watching the wolf watching Red Riding Cas.  
TBC


	2. The Wolf's Lair

Dean couldn’t get a clear shot of Cas with his high powered specialty Woodsmen binoculars. He had them set to “stalker” but that still didn’t help. He thought maybe if that tall drink of manimal would move his furry butt he could see much better.  
“Pssst…hey pervert wolf move your well formed ass I can’t see anything!”  
Sam trailed his nose through the air and his ears perked up, “Mmm…is that delicious Dean I smell?”  
“It’s Sexy Dean and yeah it’s me.” He smelled his armpit, “Sorry about that.”  
Sam sauntered over in tight leather chaps sans pants or underwear and black leather boots with silver chains. He wore a t shirt that said “Bad Boy” in black letters and it was cropped right under his nipples showing off his abs.  
Dean was wearing flannel, not very impressive.  
Sam circled him poking and prodding his flesh with long fingers, “Do you own anything besides flannel and denim?”  
“Sorry, the lumberjack camp is short on designer clothes plus I don’t feel the need to dress like a fancy boy to get what I want.”  
Sam suddenly swooped in wrapping his arms around Dean and dipping him to the forest floor. He ran his very long tongue along the woodsman’s neck lingering on his pulse, “Delicious…I would so love to eat you.”  
Dean tried to push him away but there was no use, “Come one man, I just wanted to masturbate over the little cutie on the couch in there. Can’t a guy jack it in the bushes without getting molested?”  
Sam grabbed the binoculars, “Impressive, you have the Woodsmen brand and its set the “stalker.” Sam looked through them and sure enough he could zero in on Cas and his little red shorts catching a glimpse of his goodies falling out the side.  
“Nice!”  
Dean righted himself and took a look, “Wow, that little guy is sure packing isn’t he?”  
Sam growled, “He’s mine!”  
Dean growled back, “No way, I saw him first. Besides you sleep with everybody, you don’t need him.”  
“I don’t sleep with everyone, only good looking boys.”  
They both heard a shotgun racking, there was Grandpa Bobby pointing it right at both of them, “You all got till the count of five to get away from my cottage and stop lusting after my little bitty, innocent grandson.”  
Sam snapped, “If he doesn’t want to get banged he shouldn’t prance around in those porno shorts of his!”  
“They aren’t porno shorts; besides you can’t take advantage of a fella just because he likes tight clothes. One.”  
Dean held up his hands and smiled at Bobby, “Look I swear I only have honorable intentions.”  
“Oh really, that’s why your prowlin’ around here during my Golden Girls marathon? Two.”  
Sam grabbed his junk and gave it a squeeze, “I got something for your cock tease grandson old man.”  
“Keep it to yourself you furry weirdo! Three.”  
Dean tried again, “I want to court him, look he could do worse than me. I have a cabin with indoor plumbing!”  
“Keep your plumbing away from Cas, Dean the Sexy Woodsman. Four.”  
Sam gave Bobby a big, toothy grin, “It’s his official title.”  
“Holy shit wolf Sam I think he’s really going to shoot!”  
The pair scurried into the woods just as Bobby yelled, “Five!”  
………………..  
Dean walked into the cave with Sam against his better judgment but the night was cold and the rain was heavy. He looked around very surprised at how nice the wolf den was.  
The focal point was the bed, a huge, heart shaped affair with silk sheets, velvet pillows and little cherubs carved into the headboard. On the end table was a huge basket of sex toys and a selection of lubricants.  
“Nice digs, I take it you bring a lot of tail back here.” Dean snickered at his own joke.  
Sam leered at Dean, “I plan to get some tail…strip for me hot stuff.”  
Dean tried to leave the cave but the huge wolf blocked his way, Sam pushed him all the way over to the heart shaped bed and tore off Deans clothing. It took awhile to get through that many layers of flannel but finally the wolf was rewarded with the best set of nipples he ever saw.  
“Wow, those are great nipples!”  
Dean tweaked them, “Yup, I have superior nipples. Tell me something I don’t know jackass.”  
“You’re about to get nine inches of wolf, you didn’t know that did you?”  
Dean crawled across the bed slipping right out of the wolfs big paws, “No way, I’m not into bestiality!” Sam leaped on his back and wrenched his legs open, “I’m a manimal not an animal get that pretty ass back here!”  
He flipped Dean on his back and got him ankles to ears, “You are going to love it I promise. I always take care of my boys needs first; I’ll eat you right up.”  
Dean struggled as the Sam licked his way down, “Help…Help! A wolf is…oh…yeah that’s…wow you sure know how to eat a guy…holy…guhguhaaaaah!”  
Sam knew the incoherent last part mean he was really going to be eating something real soon. Sure enough Dean let loose as the wolf greedily drank it all down.  
He rode Dean after that, long and hard. Dean wouldn’t walk right for a week after that night but it was totally worth it.  
Afterward they cuddled a bit and Sam allowed Dean to sleep over.  
……………….  
Dean woke up to breakfast in bed, “Here you go champ, eat up and then hit the road.”  
Dean looked down at the tray of food then to the greatest lover in the world, “Rude!”  
Sam shrugged, “Hey you got to sleep over and you get fed. I don’t do that for just anyone. Now eat then go do whatever it is woodmen do, I’m busy.”  
Dean gobbled his food down, got dressed and hit the road back to the lumberjack camp hoping Cas might come skipping by.  
He grumbled on the way there, “Damn short sex scene, I wish the writer would throw me a bone.” Then he giggled at his double entendre. “You are sooo clever Winchester, definitely main character material!”  
A voice boomed from the clouds, “Next story, get over it!”  
Dean looked up with a look of fright on his face, “God…is that you?”  
“If it will stop your whining sure why not, now run along and stop bitching.”  
“Yes ma’am!”  
………………  
Cas sat in the sunny kitchen eating pancakes with his grandfather, “Grandpa can I ask you something?”  
Bobby was dumping cold medicine in his coffee, “Yeah kid what?”  
“I was thinking that intercourse would be sort of fun. I get morning wood all the time and take care of it myself but still I bet relations with…say a big bad wolf might be interesting.”  
“First off I don’t want to hear you just wacked off in the guest room…”  
“I washed the sheets!”  
“Whatever, secondly Sam wolf is bad! He doesn’t want a relationship with anyone and you’re a virtuous little fella so keep those tiny red shorts of yours up ok?”  
Cas frowned down at his pancakes, “Ok grandpa.”  
Bobby pointed to the pancakes, “Eat, your too damn skinny as it is. I’m glad you’re giving up this wolf sex idea, that’s all we need is a litter of manimal pups around here.”  
Cas had a surprised look upon hearing that, “I can get pregnant from rump sex with a wolf man?”  
“Of course, it’s a fairytale. Anything can happen in a fairytale!”  
……………  
Sam dressed in tight jeans and a nice pinstripe dress shirt; he picked a dozen roses from his garden and headed out to meet Cas on his way home.  
TBC


	3. No Means No!

Bobby stood there clutching his hands together as he watched his only grandchild tug the tiniest red shorts in the universe out of his ass crack. “Remember what I said about men and wolves Cas, they are all bad news to a little fella like you.”  
Cas gave his grandpa a big smile, “Don’t worry I remember, don’t let them touch my butt.”  
Bobby patted his head, “Good boy Cas, just remember that and you will be ok.” He looked out the window and was relieved the morning was fair and the path outside the cottage looked free of perverts but that didn’t mean much. “Are you sure you don’t want me to walk you home?”  
Cas tucked the empty basket under his arm and headed out, waving as he went, “No thanks, I’m a big boy.”  
Bobby clung to the heavy oak door watching Cas skip away, “Poor kid is gonna get molested I just know it. He’s got perv bait written all over him.”  
…………….  
Sam was casually leaning on a large pine tree holding a bouquet of roses when Cas happened by. He spotted the wolf and cautiously gave Sam a wide berth. Cas fingered the can of bear mace on his utility belt right next to his stun gun.  
Sam hurried over and thrust the flowers at Cas, “Pretty flowers for a very pretty boy.”  
Cas took the roses, “They are lovely, thank you Sam Wolf but now I must hurry home to mother.” It was hard to resist Sam; he was dressed as a proper gentleman with a silk top hat complete with ear holes cut out. He wore a dapper dove grey suit with a pale pink tie and diamond tie tack to match his earring.  
Sam bent down and came nose to nose with little Cas, “Why in such a hurry? I would so enjoy showing you around the forest.” He tried so hard to be good this time but a wolf can’t change overnight. “I’d like to show you around my den…especially my bed and then eat your butt for hours,” his tongue flicked the tip of Cas’ nose, “until your virgin passage is nice and loose.”  
Cas unleashed a spray of bear mace right in Sam’s eyes then kicked him in the crotch with his sneaker and screamed, “No means no!”   
Sam rolled around on the ground holding his balls with one hand and rubbing his eyes with the other. He howled in pain and cursed little red riding Cas for what he had done.  
Cas skipped quickly away as Sam snarled, “I’ll get you, my pretty, and your little butt too!”  
……………..  
Cas pranced through the lumberjack camp which was out of his way a bit but he so enjoyed the compliments the big, burly men yelled at him.  
“I got twelve inches but I don’t use it as a rule. For you I’ll make an exception.”  
“We wanna pull a train on your caboose.”  
“I got a log for your dam.”  
And so forth and so on, the less imaginative lumberjacks simply yelled, “I want to have sex with you.”   
He was also called, candy ass, spinner boy, booty bait, hot pants, cock tease, little balls blue, twinkie dink and jail bait. Of course Cas simply smiled at them all, gave a happy wave and kept on skipping.  
Someday his forays into the lumberjack camp would end in disaster.  
……………………  
Cas ran into their humble cottage and slammed the door behind him. His mother hurried out to see what the commotion was, “Darling you look terrified!”  
“Mother a wolf wants to eat me!”  
“Eat you?”  
“Yes, eat my butt, I find that offensive and wasteful!”  
Lupa set a plate of cookies and a glass of milk in front of her sweet but clueless son. She sat down and gave Cas all her attention, “Ok I’ll bite, what do you mean by wasteful?”  
Cas frowned in that adorable way of his as he played with a button on his blouse, “If I were a predator I would eat all of my prey not just its butt. The wolf spoke of virgin loose passages and all sorts of odd things I didn’t understand.”  
She reached over and held his hand, “Honey did grandpa talk to you about being careful around men and wolves?”  
“Yes.”  
Lupa gave her son just about the same frown, “Did you prance through that damn lumberjack camp again?”  
“Yes…but mother they are always very friendly to me.”  
She sighed in frustration, “Milk carton…just like I predicted. You and I need to have a long talk young man.”  
……………..  
Sam had a pretty thing bouncing on his cock enthusiastically and although the sex was wonderful it still didn’t have that mating sort of feel he was looking for. He just knew if he could get Cas in the sack that Sam would have a raucous good time.   
The blonde ejaculated over the wolfs cut abs as he moaned, “Mister Wolf you are sooo big!”   
Sam watched the limber blonde practically spring right off from his dick he was so eager to please, “Why thank you sweet little Timothy, hang on because I’m about to wrap this up.” He lifted the boy up high with his hips and emptied his balls inside the tight channel.  
Timothy collapsed on top of Sam who pushed the former virgin off onto his half of the silk bedding. “Time to wrap it up kid, I don’t let anyone sleep over. Its school tomorrow and I won’t be the downfall of your education.”  
Timothy walked his fingers down to the wolfs furry treasure trail, “Silly Mister Wolf, its summertime! I don’t start…”  
Sam clamped a hand over his pouty, pink lips, “Stop, don’t tell me what grade you’re in.”   
Timothy was in a pouty mood, “Age is just a number.”  
“Yeah well in your case 16 will get me 20. Get dressed and hit the road.”  
Timothy grumbled as he got dressed, “Fine…gotta pick out my Catholic school uniform for next month anyway.”  
Sam was twitching down below at the thought of Timothy wearing little navy shorts, a white shirt and plaid tie, “Seriously, you are going to Catholic school?”  
He grabbed his well worn book bag with “St. Peter Prep” embroidered on it, “I’m never coming back here!” Sam countered with, “Fine, I already got your virginity so I don’t care!”  
Timothy stalked to the door with a parting jab, “They should just call you “Bad Wolf” and leave the word “big” out of it!”  
“Don’t let the door hit your deflowered ass on the way out Peter Prep!” When Sam stood Timothy squeaked like a mouse and scurried out the door.  
Sam flopped backward on the bed dramatically even though there was no one to see him. He picked up his princess phone and dialed his sister, Charlie the Slightly Bad Wolf and invited her over to give him a ladies point of view because after all, in Sam’s eyes, Cas was a bitch.  
A short while later a petite wolf wearing black jeans and boots, a low slung studded belt and a tank top with Hello Kitty on the front stepped inside. “Hey loser its Charlie where are you?”  
Her furry ginger ears perked up when she heard moaning and in the boudoir she found her brother Sam eating a quart of Hagen Paws ice cream in Vanilla Virgin flavor. “Good heavens man, you look like crap!”  
Sam took another lick of the frozen confection and looked up at her with big, sad eyes, “Sister I need help.”  
TBC

A/N I do not own any part of nor am making money off Hello Kitty, any particular ice cream brand, Supernatural characters referenced or anything else in this chapter.


	4. Sequins & Bourbon

Lupa had Cas tucked into to his hand hewn bed, a lovely gift from a secret admirer from the lumberjack camp. The boy was pink cheeked from a nice hot bath and was cuddled up with a cozy quilt and a secreted copy of Honcho magazine.  
Cas stole it from a sticky floored men’s toilet at a gas station in the village. Never mind that there wasn’t a car anywhere, the gas station survived on its beer and dirty magazine sales.  
“Sweetheart, mommy needs to school you on the evils of men and wolves.”  
Cas was reading an article under the blanket with a flashlight, it was titled, “Cut or Uncut?” Lupa tugged down the quilt and snatched away the magazine, “See, this is what I mean. You get all your information about sex via defunct gay porn magazines.”  
Cas lifted the blanket and frowned, “I’m cut according to the article, my penis no longer wears a turtleneck.”  
His mother gasped, “Honestly, what is wrong with you?”  
He grinned at her, “I’m a precocious boy.”  
Lupa patted his cheek and smiled sweetly at her son, “Don’t be a smartass …anyway you know they are only interested in you for your virgin charms.”  
Cas took a flower from the vase on his nightstand, he ran one of the rose petals over his cheek, “The wolf gave me roses, I sprayed him with bear mace after he said he would eat me. Now I feel bad for doing that.”  
She looked out the window at the full moon appearing from behind a trail of drifting clouds. Lupa rubbed her sweaty palms on her apron and stood up, “I’ll let you sleep and we can talk in the morning before I send you to grandpa with more medicine and goodies.”  
……………..  
Sam moaned, “What is wrong with me? I want that hot little bitch so bad it’s all I can think about day and night. I’ve barely met my virgin quota this week, my dick is just not into it.”  
Charlie slapped her big brother across the face. That was no easy feat without a stepladder. “Snap out of it!”  
“Damn it Charlie that hurt like hell, why did you do that?!”  
“I saw it in a movie.”  
Sam now had an audience so he swooned onto his heart shaped shag bed, “Charlie I don’t even hang out at the high school or soccer camp anymore. Why just last week there was a group of teens camping with their scoutmaster and I didn’t go after a single one.”  
He dabbed his eyes with a hanky, “I even crashed a meeting of young men taking a virginity pledge at a local church last week and by the time I left over half still remained intact.”  
Now Charlie was truly worried, she pressed her hand to Sam’s forehead, “No fever…oh this is bad Sammy. You have lost your edge, if you don’t bang this tidbit soon I think your reputation will be ruined.”  
Sam flipped on his stomach and humped a pillow, “Sorry, I just think about him and I…I…oh yeah!”   
Charlie wrinkled her nose, “Gross.”  
Sam sat up with a pink, furry pillow on his lap to hide the wet spot, “Plus I have to worry about all those creepy lumberjacks getting that ass first. Especially this one called Dean,” the wolf ran his long tongue over his lips, “I popped his cherry reeeeal good.”  
He started cackling as if the memory was the funniest thing in the world.  
Now Charlie’s furry little ears perked up, “Oh this Dean sounds nice, tell me more.”  
His face light up while describing the woodsman, “Hot, so smokin’ hot you wouldn’t believe it! A nice, firm bubble butt, you know the kind. He has big green eyes, thick lashes, perky nipples…”  
Charlie rolled her eyes, “Yes Sam I get it but what about his privates?”  
Sam pushed the pillow tightly to his groin, “Full balls, thick long dick and nice soft curls crowning it all.” His eyes rolled back in his head as a shudder ran through him, “Sorry.”  
“Gross.”  
That night Charlie helped Sam devise a plan to deflower Cas. She left after several beers, planning on stopping over at Goldilocks house to give the pretty blonde virgin a good old fashion wolf licking and a finger bang. Yes, Charlie was as perverted as her brother.  
……………..  
Cas was sitting there at the breakfast table humming a little tune as he swung his feet back and forth. His mother placed a bowl of porridge in front of him then patted his head, “Why are you so cheerful this morning?”  
He swiveled toward her and stuck out his legs, “I have my new white knee socks on plus my new red shorts.” He stood and flashed his fanny, the shorts were even tinier than the ones he usually wore and on each back pocket was a sequined red heart.  
“Cas those are obscene!”  
He wiggled a bit then sat back down, “I know, but I’m a big boy now mother and I can handle myself. I like glittery things and showing off my butt, I refuse to dress down so I’m not molested.”  
Lupa slid the basket of goodies toward her son, “Fine, don’t come crying to me when you got a belly full of pups…I mean babies.”  
He grabbed the basket, “You worry too much. Have a nice day mother. I am going to stay over at grandpas again.” Cas kissed her cheek and pranced out the door.  
……………….  
Bobby stood at the door with a shotgun, “Who is it?”  
“Candygram.”  
“Oh no, I’m not getting’ fooled by that again.”  
Sam had no idea what he was talking about since the wolf wasn’t fond of old SNL skits.  
“Pizza delivery.”  
Bobby pulled out his wallet, “Well that’s more like it!” Never mind that Bobby hadn’t ordered a pizza. He unlocked the door and Sam immediately rushed in, he lifted Bobby and slammed him into the wall.   
“Ok old man this is how it’s going to go, I got you a ticket to Albuquerque. You are getting on that bus and not coming back for a week. That will give me plenty of time.”  
Bobby struggled enough so that Sam finally put him down, “Enough time for what?”  
Sam made a thrusting motion with his hips, “Time enough to deflower that hot little ticket you call your grandson.”  
“Oh no you don’t, I’m not lettin’ any skeevy wolf rape my grandson!”  
Stroked his fingers up the furry length of one ear, “Don’t worry pops, he wants me because I’m sex on two legs…or four depending on the night.”  
Bobby folded his arms in a show of defiance, “And what if I don’t go?”  
Sam snarled, “If you don’t I will see to it that Cas is eaten with my teeth and not my tongue which I can assure you feels much better.”  
Bobby knew wolves always kept their word unlike bears, he nodded and thrust out his hand, “Shake on it, promise that no harm will come to him. I figure that kid is going to put out sooner or later and I don’t want him catchin’ Lumberjack Disease.”  
The wolf frowned, “What is Lumberjack Disease?”  
“Syphilis.”   
Sam grabbed his crotch as if he could diagnose himself just from touching, “Gross, I banged a woodsman named Dean that lives with the lumberjacks!”  
Bobby let out a chuckle, “Mister Wolf…”  
“Call me Sam.”  
“Sam, everyone knows Dean the Sexy Woodsman …his official title, would never have intimate relations with a lumberjack so don’t worry. Plus between you and me, I think that kid is virgin.”  
Sam snickered, “No anymore.”  
……………  
Cas skipped through the lumberjack camp on his way to grandpa’s house. When the lonely men got a gander at his flashy new sequin shorts that hardly covered his ass the catcalls filled the forest.   
They were not imaginative at all much to Cas’ disappointment, the best was from a large ginger man called Ginger Jack, “Hey you want a hotdog to go with those buns?”  
Cas bent over to tie his sneaker, giving the oldest lumberjack Snuffy a heart attack. The raw power of a well formed booty stuffed in sequined red hot shorts was too much for the old man.   
The group watched Cas skip away. Ginger Jack was holding the now deceased Snuffy in his arms, “Well at least he died happy.”  
…………..  
Bobby put on his ball cap, grabbed his battered old suitcase and took his bus ticket, “Well off I go, remember your promise. No harm will come to little Cas right?”  
Sam was dressed in one of Bobby’s nightshirts that hit him only to the thigh; he was wearing a sleeping cap to cover his ears and had on a little pair of gold wire reading glasses.   
“I promise, so how do I look?”  
“Not like me that’s for sure but then Cas is a bit…how should I put in nicely, clueless. I suppose so he won’t notice.”  
Sam watched Bobby leave and as soon as the door closed the wolf ran to the bedroom and go right under the quilt to wait for his prey.  
…………….  
Cas stopped at the bend in the path where Sam usually hung out but this day the path was empty. he stomped his sneaker in frustration, “Darn wolf! I wore sparkles for nothing.”  
Once he got to his destination Cas knocked on the door, “Grandpa Bobby it’s me Cas, I brought you some goodies.”  
A raspy voice called out, “Come in dear and make yourself at home.”  
Cas entered and set the basket on the table, he named off some of the delicacies his mother lovingly packed for her father, “Mother packed beer nuts, Jiffy Pop, Skoal chewing tobacco…oh she even but some jerky in here and some cookies!”  
The next thing he pulled out was a bottle of Wild Turkey Kentucky bourbon. Lupa didn’t bother masking the booze this time. “Grandpa I found a bottle of Wild Turkey in here but she forgot to pack your medicine.”   
The voice came from the bedroom again, “Bring that bottle of Wild Turkey in here and come cuddle with grandpa. We can have drinks and a little fun.”  
Cas thought that was a bit weird but he grabbed the bottle and headed toward his destiny, he just hoped grandpa didn’t want to play Boggle.   
TBC


	5. Itty Bitty Bang Bang

Cas pranced slowly toward the bed, even though prancing is usually done quickly the talented little cock tease had mastered the art of prancing as well as skipping at various paces to express emotion. It was also a great work out and reason why his fanny was so toned and delicious.  
The shadowy figure that looked much bigger than grandpa reached out and beckoned to him, “Come here Cas, come sit by me and I’ll let you have a sip of Wild Turkey for being a good boy. First will you tend the fire?”  
Cas handed the bottle over then took a fireplace poker and moved the embers about, “Grandpa I think you need more wood.”  
A deep laugh came from the shadows, “Grandpa has plenty of wood right now…would you like to see?” Cas looked out the window, “No I can see the woodpile from here.”   
He bent over and stuck his hands in the wood box, “Oh you have one big log, let me stoke your fire!”   
Sam was about ready to burst, he got full glitter butt as Little Red Riding Cas bent over and everything he said sounded like a filthy innuendo. “Baby you got no idea how big my log is and you can surely stoke any man’s fire.”  
Cas giggled, “you talk funny.” He dropped the log on the fire then straightened up, “All done.”  
He hopped on the bed and got a better look at grandpa as the fire grew and filled the room with flickering of light. Sam’s face became clearer and Cas let out a gasp, “Grandpa what big eyes you have.”  
Sam opened them even wider, “The better to see your booty with my dear.”  
Cas was now a bit closer, he pull off the sleeping cap and two fuzzy ears popped out, “Grandpa what big ears you have.”  
“The better to hear your moans of pleasure with my dear.”  
Cas touched the wolfs nose, “What a big nose you have…”  
“Hey I don’t have a big nose!” Sam looked at the innocent expression on Cas’s face and let out a sigh of frustration, “The better to sniff your butt with my dear.”  
Cas swung a leg over Sam’s lap and leaned in to get a closer look at his teeth. “Oh, something poked me!”  
Sam grabbed him tight, tore off the Virgin Keeper 3000 utility belt Cas was wearing and tossed it in the fire. “It is I, Sam the wolf!”  
Cas flailed his arms around trying to get away but the more he wiggled the harder he was poked, “Help!”  
Sam ripped the clothing right off Cas then flipped him around and bent the struggling boy over. The wolf ran his nose up the crack of the little butt then gave it a tentative lick, “You are even tastier than I thought.” He began lapping at the almost impossibly tight pucker and soon his captive relaxed.  
“Oh mister wolf that feels wonderful, is that what you meant by eating me?”  
Sam didn’t bother to answer; he was too busy jamming his long, wet tongue deep inside his prey. Cas pressed his face into a decorative pillow and let out a muffled moan of ecstasy.  
Sam popped out his tongue, took a drink of Wild Turkey then cracked Cas on the rump, “Ready to get rid of that pesky virginity?”   
Cas rolled on his back and opened his legs, “You won’t hurt me will you? I’m scared to do this although I’ve thought if it often.”  
Sam knelt between the virgin’s legs while taking long strokes down his cock, “I’m afraid it will hurt a bit but I’ve opened you as much as I could. You are truly the tightest little thing I’ve ever encountered.”  
Cas looked up at the wolf with big blue eyes reminiscent of a Siamese kitten, “I trust you.”  
The wolf’s shoulders slumped. “Damn it, when you look at me that way and then say you trust me…well it takes all the fun out of it. I’m not a romantic, those roses were just to get laid you know.”  
Cas covered his face with the decorative pillow, “Now I feel stupid. I thought you wanted a boyfriend.”  
Sam snatched the pillow away, bent down and kissed him hard shoving his tongue into Cas’ mouth. The boy turned his head and sputtered, “Gross that was in my butt.”  
The wolf had lost all his patience, “I rinsed my mouth with booze you little sap.” He raised the boy’s legs up, bent him ankles to ears and shoved his cock inside. Cas let out a scream, “I’m being torn in half!”  
Sam pressed former virgin’s legs down and pinned him there, “It’s best to get inside quickly when my prey is struggling. Now my dear you are officially deflowered.”  
…………  
Dean had followed Cas to grandpa’s house hoping to make a wood delivery in the middle of the night when he heard a strangely deep but yet girly voice crying out in pain and then it slowly changed to something sounding like pleasure.  
The woodsman took his mighty Doc Marten rigger work boot and kicked the door off its hinges. It was unlocked and slightly ajar but Dean was determined to break in his new footwear.  
“Don’t worry Cas I’ll save you!”  
Dean burst into the bedroom after kicking that door down as well, then froze on the spot when he saw the scene before him. Little Cas was now riding Sam’s big cock like a pony ride at the village carnival.   
He stared transfixed at the spread cheeks rising up then sliding back down as Cas let out noises of discomfort mixed with happiness. Cas looked over his shoulder and smiled at the woodsman, “Look Dean, I’m not a virgin anymore.”  
Sam leaned around him and gave the woodsman a toothy grin, “Yeah, look Dean; he’s not a virgin anymore.” Then the wolf began to snicker.  
That snapped Dean out of his state, “Oh that’s it wolf, it is on now!”  
Sam grabbed Cas by the hips and slammed up into him, emitting a long howl as he emptied inside of the boy claiming Cas as his own now and Dean was too late.  
Dean watched as Cas slid off and flopped on his back panting like a dog on a hot summer day. “Well this sucks, I had designs on him Sam and you knew I did.”  
Sam stuck a finger in the sore butthole of his young lover, pulled it out and then sucked off the fluids. “I’m sorry about that woodsman, perhaps you would like to join us for another round.”  
Cas tried to escape but the wolf grabbed his ankle, “Where are you going little one?”  
“I don’t want to be in a wolf and woodsman sandwich, its sounds painful and my rump is very chafed.”  
Sam pushed him on his stomach and parted Cas’ butt cheeks with his big paws to show Dean what he was missing. “Come on Dean, don’t tell me this isn’t appealing to you.”  
Dean ran his tongue over his plump lips, “I bet it’s tight.”  
Sam bent down and licked the swollen flesh, “Very tight.”  
Cas struggled halfheartedly under the big predator, “Hey, do I get a say in this?”  
Both answered, “No!”  
……………..  
Sam slapped his dick across the blue eyed honeys lips, “Ok, Cas this is what you call a spit roast. You suck my cock and Dean screws you, then afterward we switch places.”  
Cas looked up at the wolf hopefully, “Oh then I get to put my penis in your butt?”  
“No.”  
“Well that doesn’t seem fair.”  
Dean, who was already poking the head of his cock at the tight hole let loose with a volley of slaps to the boy’s ass, “Life isn’t fair baby cakes.”  
Soon the three were sucking, thrusting, and making noises so loud that the woodland creatures fled. Cas had his mouth full so he didn’t make much noise at all except for a bit of gagging.  
At one point costumes were trotted out and Cas played rump ranger on Dean, he pinched the woodsman’s nipple and yelled, “Yee-haw, I’m plum full up on stallion dick!”  
It honestly didn’t take very long for the formerly innocent boy to wallow in the filth and depravity of the wolf and woodsman. In fact at one point Sam and Dean laid there exhausted, and Cas hustled in from the kitchen with big glasses of ice water so the pair could rehydrate and get back to sexy time.  
Sam watched as Cas did a nudie dance for them, he whispered to Dean, “Seriously, I’ve never had anyone wear me out before.”  
“Dude look out, the kid is heading our way and he’s holding two ball gags and a leather paddle…is that for us or him?”  
Cas crawled onto the end of the bed and tossed the ball gag to Sam, “Alright it’s my turn, put those on each other then both of you get on all fours so I can spank your pretty bums properly.”  
Dean looked at him with desperation, “Come on Cas this isn’t fair, cut us some slack.” The little guy was fastening on a pair of leather chaps and hopped back on the bed whirling the paddle above his head, “Someone once told me life isn’t fair.” Then he let out a creepy giggle.  
……………  
This ménage a trios went on for the entire week while Bobby was gone. Upon his arrival back the man was faced with two busted down doors, a mountain of pizza boxes and takeout containers plus whiskey and beer bottles tossed on the floor of almost every room.  
Nothing went unsullied; every stick of furniture, including the kitchen table was defiled by the trio’s dirty romps. Bobby went from room to room opening up windows until he came to his bedroom where Sam, Dean and Cas were laying in a tangled pile of sticky flesh.  
Bobby pulled open the curtains and windows then kicked the mattress, “Alright you filthy ingrates, do you mind telling me what my little grandson is doing with the likes of you two?”  
Dean and Sam were now awake, wide eyed and clinging to each other for dear life. Cas pulled his cheek off Sam’s lap and it made a wet sound as it separated from the spent dick beneath it, “Hi grandpa, did you have a good vacation?”  
Dean, with Sam right behind him grabbed clothing hoping it was his and the pair scrambled for the door as Bobby went to get the shotgun.  
…………….  
Four Months Later  
Lupa was kneeling next to her son as he emptied his breakfast into the toilet. He had been sick for awhile now and after hearing what happened with the wolf and the woodsman, Lupa had an idea of what was happening.  
“Cas we need to talk.”  
He sat back against wall looking at his mother with red, watery eyes, “What about?”  
“I believe you are pregnant and from the time you had your little lapse in judgment with those two ner’er-do-wells that would put you at four months along.”  
Cas moaned over his plight not know what he was going to do. “Mother I can’t be pregnant; my dream is to open an Arthur Murray Prance Studio.”  
“Well it gets worse; we don’t know who the father is. Since Sam is a wolf both of them could have gotten you in a family way.”  
……………  
Sam was entertaining several college freshmen from the swim team when Cas marched into his den, “I have to talk to you, get your dick out of that guys butt and kick them out!”  
After booting out the tender morsels Sam sat next to Cas on the heart shaped bed, “You are a rude boy, what do you want?”  
Cas laid back, lifted his blouse and a nice little belly was growing over the waistband of the horrible stretch shorts he was forced to wear. “I’ve got a problem.”  
Sam snapped the elastic on the shorts and chuckled, “I’d say, you lost your fashion sense and you’re getting plump.”  
“I’m pregnant!”  
Sam growled, “They aren’t mine.”  
Cas sat up and kicked him with his sneaker, “Darn right they are yours and I’m not going to be a single mother.”   
Dean received exactly the same visit from Cas, complete with a kick to his shin.  
…………………  
Nine Months After the Sex Romp  
Cas sat up in bed nursing two babies at a time, there were a total of three, one quite human and belonging to the woodsman and two belonging to the wolf.  
Dean and Cas paced the living room waiting for the news, Lupa stepped out and announced, “One human two wolf.”  
Dean did a fist pump and began laughing at Sam, “You lose! Gotta marry him now, whoever gave him the most babies gets a shotgun wedding.” He poked his head in the bedroom and took a look at his daughter, “Call her Penelope, I’ll send child support and we can set up visitation. See yah!”  
And with that the woodsman left.  
………………….  
Little Red Riding Cas and Sam Wolf were married and the family moved to an actual cottage in the darkest part of the forest. The young couple was happy for the most part.  
Sam changed his ways much to the chagrin of every pretty young male around. Now they had to learn about sex and lose their virginities the old fashion way, trial and error in the back of a hay wagon.  
Sam was a good husband, he was sure to give Cas sweet lovin’ almost every night.   
Charlie was pleased to be an auntie even to the human. She often watched Penelope, Wolfgang and Vincent at the house she shared with Goldilocks.  
As for Little Red Riding Cas he did open up that prance studio and taught boys from all around to express their emotions through prance then eventually graduating to advanced skip.  
Dean the Sexy Woodsman kept his word and send money for Penelope each week. Every once in awhile the trio would get together and screw like rabbits. They had a howling good time.

The End


End file.
